Just ask him. You would be surprised how many boys would be interested to try some girly clothes on if given the chance.
I talked my bf into letting me do his nails a bright pink just by asking. When I was done, we both giggled a bit, and I offered to do matching lipstick, which he accepted. Eventually I had him all decked out in a floral sundress!
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Well i personly think you should do a sexy talk like i think it would be sexy if u wore a thong.